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Synthesis 1997; 1997(10): 1143-1145
DOI: 10.1055/s-1997-1327
short paper
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New and Convenient Synthesis of 3-Methylenepent-4-enoic Acid by Electrochemical Carboxylation

Masao Tokuda* , Akihiro Yoshikawa, Hiroshi Suginome, Hisanori Senboku
  • *Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060, Japan, Fax +81(11)7066598; E-mail: tokuda@organ.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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Electrochemical carboxylation of 2-bromomethyl-1,3-dibromobut-2-ene (1) with atmospheric carbon dioxide in a DMF solution containing Bu4NI with a platinum cathode and a manganin or nickel anode gave 3-methylenepent-4-enoic acid (3) in 57% yield. The acid 3 can be used as a diene in an aqueous intermolecular Diels-Alder reaction with dimethyl fumarate to give the adduct 7 in 67% yield.

isoprenylation - isoprenyl anion - electrochemical carboxylation - carbon dioxide - Diels-Alder reaction